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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 7| July 2013| Pages m376-m377
https://doi.org/10.1107/S1600536813015456

cis-(1,4,8,11-Tetra­aza­cyclo­tetra­decane-κN4)bis­(­thio­cyanato-κN)chromium(III) thio­cyanate

Dohyun Moon,a Jong-Ha Choi,b* Keon Sang Ryoob and Yong Pyo Hongb

aPohang Accelerator Laboratory, POSTECH, Pohang 790-784, Republic of Korea, and bDepartment of Chemistry, Andong National University, Andong 760-749, Republic of Korea
*Correspondence e-mail: jhchoi@andong.ac.kr

(Received 31 May 2013; accepted 4 June 2013; online 12 June 2013)

The crystal structure of [Cr(NCS)2(cyclam)]NCS (cyclam = 1,4,8,11-tetra­aza­cyclo­tetra­deca­ne, C10H24N4) has been determined by using synchrotron radiation at 98 K. The CrIII atom is in a slightly distorted octa­hedral environment with four N atoms of the macrocyclic ligand and two N-coordinated NCS− anions in cis positions. The average Cr—N(cyclam) and Cr—NCS bond lengths are 2.085 (5) and 1.996 (15) Å, respectively. In the crystal, the uncoordinating SCN− anion is hydrogen bonded through N—H⋯S and N—H⋯N inter­actions to neighbouring complex cations.

Related literature

For the synthesis, see: Ferguson & Tobe (1970[Ferguson, J. & Tobe, M. L. (1970). Inorg. Chim. Acta 4, 109-112.]); For spectroscopic studies, see: Choi & Park (2003[Choi, J. H. & Park, Y. U. (2003). Bull. Korean Chem. Soc. 24, 384-388.]); Poon & Pun (1980[Poon, C. K. & Pun, K. C. (1980). Inorg. Chem. 19, 568-569.]). For related structures, see: Forsellini et al. (1986[Forsellini, E., Parasassi, T., Bombieri, G., Tobe, M. L. & Sosa, M. E. (1986). Acta Cryst. C42, 563-565.]); Friesen et al. (1997[Friesen, D. A., Quail, J. W., Waltz, W. L. & Nashiem, R. E. (1997). Acta Cryst. C53, 687-691.]); Meyer et al. (1998[Meyer, K., Bendix, J., Bill, E., Weyhermüller, T. & Weighardt, K. (1998). Inorg. Chem. 37, 5180-5188.]); Choi et al. (2004a[Choi, J.-H., Oh, I.-G., Lim, W.-T. & Park, K.-M. (2004a). Acta Cryst. C60, m238-m240.],b[Choi, J. H., Oh, I. G., Suzuki, T. & Kaizaki, S. (2004b). J. Mol. Struct. 694, 39-44.], 2009[Choi, J. H. (2009). Inorg. Chim. Acta, 362, 4231-4236.]); Subhan et al. (2011[Subhan, M. A., Choi, J. H. & Ng, S. W. (2011). Z. Anorg. Allg. Chem. 637, 2193-2197.]).

[Scheme 1]

Experimental

Crystal data

  • [Cr(NCS)2(C10H24N4)]NCS

  • Mr = 426.57

  • Monoclinic, P 21 /c

  • a = 10.590 (2) Å

  • b = 7.6970 (15) Å

  • c = 23.750 (5) Å

  • β = 94.70 (3)°

  • V = 1929.4 (7) Å3

  • Z = 4

  • Synchrotron radiation

  • λ = 0.740 Å

  • μ = 1.03 mm−1

  • T = 98 K

  • 0.01 × 0.01 × 0.01 mm
Data collection

  • ADSC Q210 CCD area-detector diffractometer

  • Absorption correction: empirical (HKL-3000 SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.988, Tmax = 0.989

  • 16587 measured reflections

  • 4727 independent reflections

  • 3998 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.085

  • S = 1.07

  • 4727 reflections

  • 234 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.46 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N1⋯S2i 0.86 (2) 2.59 (2) 3.4138 (15) 160.1 (17)
N2—H1N2⋯S4ii 0.77 (2) 2.66 (2) 3.3521 (14) 149.8 (18)
N3—H1N3⋯N7ii 0.834 (19) 2.119 (19) 2.9238 (19) 162.0 (17)
N4—H1N4⋯N7iii 0.851 (19) 2.150 (19) 2.947 (2) 155.9 (17)
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: ADSC Quantum-210 ADX (Arvai & Nielsen, 1983[Arvai, A. J. & Nielsen, C. (1983). ADSC Quantum-210 ADX. Area Detector System Corporation, Poway, CA, USA.]); cell refinement: HKL-3000 (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: HKL-3000; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]; program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]; molecular graphics: DIAMOND (Brandenburg, 2007[Brandenburg, K. (2007). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015456/lr2107sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015456/lr2107Isup2.hkl

checkCIF report


Comment top

The cyclam (1,4,8,11-tetraazacyclotetradecane) ligand is moderately flexible structure, and can adopt both planer (trans) and folded (cis) configurations (Poon & Pun, 1980). There are five conformational trans isomers for the cyclam which differ in the chirality of the sec-NH centers. The trans-I, trans-II and trans-V configurations can fold to form cis-I, cis-II and cis-V isomers, respectively (Subhan et al., 2011). Furthermore, the NCS group is an ambidentate ligand because it can coordinate to a transition metal ion through the nitrogen (M-NCS), or the sulfur (M-SCN), or both (M-NCS-M).

In this communication, we report the structure of [Cr(cyclam)(NCS)2]SCN in order to determine the mode of bonding of the thiocyanate group and to verify geometrical assignment made on the basis of spectroscopic measurements (Poon & Pun, 1980; Choi & Park (2003).

Counter anionic species play a very important role in coordination chemistry. This is another example of a cis-[Cr(cyclam)2(NCS)2]+ but with different counter anion (Friesen et al., 1997). The structural analysis shows that there is only one crystallographically independent Cr(III) complex cation where the nitrogen atoms of cyclam ligand occupy four adjacent sites and the two N-bonded NCS groups coordinate to the chromium centre in cis arrangement. The cyclam adopts the folded cis-V configuration with six- and five-membered chelate rings in chair and gauche conformation, respectively. The same conformational arrangement has been found in cis-[Cr(cyclam)(ONO)2]NO2(Choi et al., 2004a). An ellipsoid plot (50% probability level) of the cis-[Cr(cyclam)(NCS)2]SCN, together with the atomic labelling, is depicted in Fig. 1.

The Cr—N(cyclam) distances of 2.0851 (14) and 2.0897 (14) Å are good agreement with the corresponding Cr—N distances found in [Cr(cyclam)(ox)]ClO4 (Choi et al., 2004b), [Cr(cyclam)(acac)](ClO4)2 (Subhan et al. , 2011) and trans-[Cr(cyclam)(nic-O)2]ClO4 (Choi, 2009). The mean Cr-NCS distance of 1.9957 (14) Å is close the value of the range 1.9827 (15)–1.9895 (16) Å found in trans-[Cr(Me2tn)2(NCS)2]SCN, but slightly longer than the 1.9698 (14) Å of Cr-ONO found in cis-[Cr(cyclam)(ONO)2]NO2 (Choi et al., 2004a). The folded angle of 97.11° in the cyclam is comparable to the corresponding angles of 98.55°, 97.03°, 95.09°, 94.51° and 92.8° in [Cr(cyclam)(ox)]ClO4, [Cr(cyclam)(acac)](ClO4)2, cis-[Cr(cyclam)(ONO)2]NO2, cis-[Cr(cyclam)(N3)2]ClO4 and cis-[Cr(cyclam)Cl2]Cl, respectively (Choi et al., 2004b; Subhan et al., 2011; Meyer et al., 1998; Forsellini et al., 1986). As usually observed, the five-membered chelate rings adopt a gauche, and six-membered ring is in the chair conformation. The average bond angles of five- and six-membered chelate rings around chromium(III) are the 83.13 (6) and 90.21 (6)°, respectively. The coordinated isothiocyanate ligands are almost linear with N—C—S angles of 179.69 (17)° and 178.83 (15)°. The uncoordinated NCS- anion also adopts a linear conformation and its N and S atoms participates in hydrogen bonds with the N—H groups of cyclam ligand. The C12—S2 and C13—S4 bond lengths [1.6232 (17) and 1.639 (2) Å] of are slightly shorter than the C11—S3 [1.6082 (17) Å] in the NCS- groups. It seems that the slight elongation of the distances are attributed to the weak H atoms bonds of both S2 and S3 atoms. Table 1 contains the distances and angles of hydrogen bonds. These hydrogen-bonded networks help to stabilize the crystal structure.

Related literature top

For the synthesis, see: Ferguson & Tobe (1970); For spectroscopic studies, see: Choi & Park (2003); Poon & Pun (1980). For related structures, see: Forsellini et al. (1986); Friesen et al. (1997) Meyer et al. (1998); Choi et al. (2004a,b, 2009); Subhan et al. (2011).

Experimental top

The free ligand cyclam was purchased from Stream Chemicals and used as provided. All chemicals were reagent grade materials and used without further purification. The cis-[Cr(cyclam)(NCS)2]SCN was synthesized according to the literature (Ferguson & Tobe, 1970).

Refinement top

Non-hydrogen atoms were refined anisotropically; hydrogen atoms were first located in a difference map; N–H hydrogen atoms were freely refined and C–H hydrogen atoms were constrained to ride on the parent carbon atom, with C–H = 0.98 Å and C–H = 0.99 Å and Uiso(H) = 1.2Ueq(C) for methylene groups.

Structure description top

The cyclam (1,4,8,11-tetraazacyclotetradecane) ligand is moderately flexible structure, and can adopt both planer (trans) and folded (cis) configurations (Poon & Pun, 1980). There are five conformational trans isomers for the cyclam which differ in the chirality of the sec-NH centers. The trans-I, trans-II and trans-V configurations can fold to form cis-I, cis-II and cis-V isomers, respectively (Subhan et al., 2011). Furthermore, the NCS group is an ambidentate ligand because it can coordinate to a transition metal ion through the nitrogen (M-NCS), or the sulfur (M-SCN), or both (M-NCS-M).

In this communication, we report the structure of [Cr(cyclam)(NCS)2]SCN in order to determine the mode of bonding of the thiocyanate group and to verify geometrical assignment made on the basis of spectroscopic measurements (Poon & Pun, 1980; Choi & Park (2003).

Counter anionic species play a very important role in coordination chemistry. This is another example of a cis-[Cr(cyclam)2(NCS)2]+ but with different counter anion (Friesen et al., 1997). The structural analysis shows that there is only one crystallographically independent Cr(III) complex cation where the nitrogen atoms of cyclam ligand occupy four adjacent sites and the two N-bonded NCS groups coordinate to the chromium centre in cis arrangement. The cyclam adopts the folded cis-V configuration with six- and five-membered chelate rings in chair and gauche conformation, respectively. The same conformational arrangement has been found in cis-[Cr(cyclam)(ONO)2]NO2(Choi et al., 2004a). An ellipsoid plot (50% probability level) of the cis-[Cr(cyclam)(NCS)2]SCN, together with the atomic labelling, is depicted in Fig. 1.

The Cr—N(cyclam) distances of 2.0851 (14) and 2.0897 (14) Å are good agreement with the corresponding Cr—N distances found in [Cr(cyclam)(ox)]ClO4 (Choi et al., 2004b), [Cr(cyclam)(acac)](ClO4)2 (Subhan et al. , 2011) and trans-[Cr(cyclam)(nic-O)2]ClO4 (Choi, 2009). The mean Cr-NCS distance of 1.9957 (14) Å is close the value of the range 1.9827 (15)–1.9895 (16) Å found in trans-[Cr(Me2tn)2(NCS)2]SCN, but slightly longer than the 1.9698 (14) Å of Cr-ONO found in cis-[Cr(cyclam)(ONO)2]NO2 (Choi et al., 2004a). The folded angle of 97.11° in the cyclam is comparable to the corresponding angles of 98.55°, 97.03°, 95.09°, 94.51° and 92.8° in [Cr(cyclam)(ox)]ClO4, [Cr(cyclam)(acac)](ClO4)2, cis-[Cr(cyclam)(ONO)2]NO2, cis-[Cr(cyclam)(N3)2]ClO4 and cis-[Cr(cyclam)Cl2]Cl, respectively (Choi et al., 2004b; Subhan et al., 2011; Meyer et al., 1998; Forsellini et al., 1986). As usually observed, the five-membered chelate rings adopt a gauche, and six-membered ring is in the chair conformation. The average bond angles of five- and six-membered chelate rings around chromium(III) are the 83.13 (6) and 90.21 (6)°, respectively. The coordinated isothiocyanate ligands are almost linear with N—C—S angles of 179.69 (17)° and 178.83 (15)°. The uncoordinated NCS- anion also adopts a linear conformation and its N and S atoms participates in hydrogen bonds with the N—H groups of cyclam ligand. The C12—S2 and C13—S4 bond lengths [1.6232 (17) and 1.639 (2) Å] of are slightly shorter than the C11—S3 [1.6082 (17) Å] in the NCS- groups. It seems that the slight elongation of the distances are attributed to the weak H atoms bonds of both S2 and S3 atoms. Table 1 contains the distances and angles of hydrogen bonds. These hydrogen-bonded networks help to stabilize the crystal structure.

For the synthesis, see: Ferguson & Tobe (1970); For spectroscopic studies, see: Choi & Park (2003); Poon & Pun (1980). For related structures, see: Forsellini et al. (1986); Friesen et al. (1997) Meyer et al. (1998); Choi et al. (2004a,b, 2009); Subhan et al. (2011).

Computing details top

Data collection: ADSC Quantum-210 ADX (Arvai & Nielsen, 1983); cell refinement: HKL-3000 (Otwinowski & Minor, 1997); data reduction: HKL-3000 (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. Perspective view (50% probablility level) of cis-[Cr(cyclam)(NCS)2]SCN
cis-(1,4,8,11-Tetraazacyclotetradecane-κN4)bis(thiocyanato-κN)chromium(III) thiocyanate top
Crystal data top
[Cr(NCS)2(C10H24N4)]NCSF(000) = 89
Mr = 426.57Dx = 1.469 Mg m−3
Monoclinic, P21/cSynchrotron radiation, λ = 0.740 Å
a = 10.590 (2) ÅCell parameters from 39021 reflections
b = 7.6970 (15) Åθ = 1.9–33.1°
c = 23.750 (5) ŵ = 1.03 mm−1
β = 94.70 (3)°T = 98 K
V = 1929.4 (7) Å3Block, pink
Z = 40.01 × 0.01 × 0.01 mm
Data collection top
ADSC Q210 CCD area-detector
diffractometer		3998 reflections with I > 2σ(I)
Radiation source: PLSII 2D bending magnetRint = 0.038
ω scanθmax = 29.5°, θmin = 2.0°
Absorption correction: empirical (using intensity measurements)
(HKL-3000 SCALEPACK; Otwinowski & Minor, 1997)		h = −14→14
Tmin = 0.988, Tmax = 0.989k = −10→10
16587 measured reflectionsl = −31→31
4727 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.0543P)2 + 0.0369P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.38 e Å−3
4727 reflectionsΔρmin = −0.46 e Å−3
234 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0149 (11)
Crystal data top
[Cr(NCS)2(C10H24N4)]NCSV = 1929.4 (7) Å3
Mr = 426.57Z = 4
Monoclinic, P21/cSynchrotron radiation, λ = 0.740 Å
a = 10.590 (2) ŵ = 1.03 mm−1
b = 7.6970 (15) ÅT = 98 K
c = 23.750 (5) Å0.01 × 0.01 × 0.01 mm
β = 94.70 (3)°
Data collection top
ADSC Q210 CCD area-detector
diffractometer		4727 independent reflections
Absorption correction: empirical (using intensity measurements)
(HKL-3000 SCALEPACK; Otwinowski & Minor, 1997)		3998 reflections with I > 2σ(I)
Tmin = 0.988, Tmax = 0.989Rint = 0.038
16587 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.38 e Å−3
4727 reflectionsΔρmin = −0.46 e Å−3
234 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cr10.78572 (2)0.65230 (3)0.13425 (2)0.01445 (9)
S20.80594 (3)1.01716 (5)0.29372 (2)0.02043 (10)
S31.17137 (4)0.91514 (6)0.09132 (2)0.03337 (12)
N10.87142 (12)0.48585 (16)0.19523 (5)0.0176 (3)
H1N10.949 (2)0.521 (2)0.2008 (8)0.030 (5)*
N20.60770 (11)0.58345 (16)0.15912 (5)0.0158 (2)
H1N20.5895 (18)0.494 (3)0.1465 (8)0.026 (5)*
N30.80817 (12)0.44123 (17)0.08083 (5)0.0194 (3)
H1N30.7441 (18)0.378 (2)0.0769 (8)0.024 (5)*
N40.67930 (12)0.78077 (18)0.06965 (5)0.0193 (3)
H1N40.6773 (17)0.888 (2)0.0783 (8)0.024 (5)*
N50.95059 (12)0.74035 (17)0.11200 (5)0.0216 (3)
N60.78208 (12)0.85015 (16)0.18914 (5)0.0203 (3)
C10.82134 (14)0.4809 (2)0.25209 (6)0.0199 (3)
H1A0.83570.59540.27050.024*
H1B0.86940.39320.27560.024*
C20.68044 (14)0.4373 (2)0.25004 (6)0.0203 (3)
H2A0.66640.32450.23050.024*
H2B0.65690.42250.28920.024*
C30.59240 (14)0.5705 (2)0.22082 (6)0.0195 (3)
H3A0.50370.53870.22630.023*
H3B0.60940.68550.23850.023*
C40.88174 (15)0.30950 (19)0.17019 (7)0.0224 (3)
H4A0.80160.24490.17280.027*
H4B0.95090.24370.19110.027*
C50.90900 (15)0.3290 (2)0.10901 (7)0.0248 (3)
H5A0.99320.38300.10640.030*
H5B0.90890.21380.09050.030*
C60.51544 (14)0.7103 (2)0.13191 (6)0.0215 (3)
H6A0.52390.82390.15140.026*
H6B0.42780.66770.13410.026*
C70.54392 (14)0.7294 (2)0.07095 (6)0.0228 (3)
H7A0.52830.61800.05070.027*
H7B0.48840.81910.05210.027*
C80.83850 (16)0.4808 (2)0.02215 (6)0.0266 (3)
H8A0.84900.37030.00170.032*
H8B0.92010.54410.02350.032*
C90.73707 (17)0.5890 (2)−0.01027 (7)0.0295 (4)
H9A0.75680.5952−0.05030.035*
H9B0.65480.5286−0.00930.035*
C100.72283 (16)0.7724 (2)0.01150 (6)0.0257 (3)
H10A0.80540.83260.01140.031*
H10B0.66140.8356−0.01470.031*
C111.04332 (14)0.81402 (19)0.10314 (6)0.0200 (3)
C120.79292 (13)0.92117 (18)0.23267 (6)0.0172 (3)
S40.56857 (4)0.72414 (6)0.36233 (2)0.03051 (12)
N70.37447 (15)0.65647 (19)0.43301 (7)0.0338 (3)
C130.45576 (15)0.68218 (19)0.40360 (7)0.0235 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.01319 (12)0.01531 (13)0.01455 (13)−0.00352 (8)−0.00060 (8)0.00023 (8)
S20.01916 (18)0.02155 (19)0.02016 (19)−0.00004 (13)−0.00094 (14)−0.00355 (14)
S30.0250 (2)0.0448 (3)0.0303 (2)−0.01871 (19)0.00255 (17)0.00597 (19)
N10.0142 (6)0.0178 (6)0.0205 (6)−0.0020 (5)−0.0012 (5)0.0014 (5)
N20.0142 (6)0.0153 (6)0.0176 (6)−0.0019 (5)0.0005 (5)−0.0001 (5)
N30.0170 (6)0.0210 (6)0.0205 (6)−0.0036 (5)0.0031 (5)−0.0031 (5)
N40.0183 (6)0.0204 (6)0.0184 (6)−0.0053 (5)−0.0028 (5)0.0018 (5)
N50.0183 (6)0.0244 (7)0.0218 (6)−0.0068 (5)0.0002 (5)0.0017 (5)
N60.0216 (6)0.0171 (6)0.0217 (6)−0.0036 (5)−0.0012 (5)−0.0002 (5)
C10.0212 (7)0.0209 (7)0.0171 (7)−0.0012 (6)−0.0019 (6)0.0035 (6)
C20.0213 (7)0.0213 (7)0.0183 (7)−0.0019 (6)0.0022 (6)0.0036 (6)
C30.0176 (7)0.0223 (7)0.0190 (7)−0.0020 (6)0.0045 (6)−0.0001 (6)
C40.0208 (7)0.0177 (7)0.0282 (8)0.0016 (6)0.0000 (6)0.0006 (6)
C50.0219 (7)0.0231 (8)0.0298 (8)0.0023 (6)0.0042 (6)−0.0043 (6)
C60.0154 (7)0.0230 (7)0.0256 (8)0.0005 (6)−0.0006 (6)0.0038 (6)
C70.0172 (7)0.0275 (8)0.0228 (7)−0.0041 (6)−0.0045 (6)0.0043 (6)
C80.0293 (8)0.0320 (9)0.0195 (7)−0.0042 (7)0.0077 (6)−0.0062 (6)
C90.0340 (9)0.0378 (9)0.0167 (7)−0.0073 (8)0.0013 (7)−0.0040 (7)
C100.0284 (8)0.0323 (9)0.0160 (7)−0.0071 (7)−0.0006 (6)0.0049 (6)
C110.0211 (7)0.0234 (7)0.0150 (7)−0.0028 (6)−0.0019 (6)0.0004 (6)
C120.0146 (6)0.0146 (6)0.0218 (7)−0.0024 (5)−0.0017 (6)0.0028 (5)
S40.0347 (2)0.0333 (2)0.0235 (2)0.01233 (18)0.00211 (17)0.00132 (17)
N70.0297 (8)0.0263 (7)0.0453 (9)0.0070 (6)0.0013 (7)0.0027 (6)
C130.0260 (8)0.0160 (7)0.0267 (8)0.0081 (6)−0.0087 (7)−0.0027 (6)
Geometric parameters (Å, º) top
Cr1—N51.9846 (13)C2—C31.515 (2)
Cr1—N62.0071 (13)C2—H2A0.9900
Cr1—N42.0781 (14)C2—H2B0.9900
Cr1—N12.0849 (13)C3—H3A0.9900
Cr1—N32.0868 (13)C3—H3B0.9900
Cr1—N22.0895 (13)C4—C51.512 (2)
S2—C121.6231 (15)C4—H4A0.9900
S3—C111.6081 (16)C4—H4B0.9900
N1—C41.4895 (19)C5—H5A0.9900
N1—C11.4913 (19)C5—H5B0.9900
N1—H1N10.86 (2)C6—C71.510 (2)
N2—C61.4904 (19)C6—H6A0.9900
N2—C31.4909 (18)C6—H6B0.9900
N2—H1N20.77 (2)C7—H7A0.9900
N3—C81.4871 (19)C7—H7B0.9900
N3—C51.489 (2)C8—C91.518 (2)
N3—H1N30.834 (19)C8—H8A0.9900
N4—C71.4901 (19)C8—H8B0.9900
N4—C101.4928 (19)C9—C101.515 (2)
N4—H1N40.851 (19)C9—H9A0.9900
N5—C111.168 (2)C9—H9B0.9900
N6—C121.1666 (19)C10—H10A0.9900
C1—C21.526 (2)C10—H10B0.9900
C1—H1A0.9900S4—C131.6384 (19)
C1—H1B0.9900N7—C131.169 (2)
N5—Cr1—N688.74 (6)H2A—C2—H2B107.5
N5—Cr1—N494.39 (5)N2—C3—C2112.52 (12)
N6—Cr1—N494.61 (6)N2—C3—H3A109.1
N5—Cr1—N193.01 (5)C2—C3—H3A109.1
N6—Cr1—N192.61 (5)N2—C3—H3B109.1
N4—Cr1—N1169.77 (5)C2—C3—H3B109.1
N5—Cr1—N387.56 (6)H3A—C3—H3B107.8
N6—Cr1—N3174.14 (5)N1—C4—C5108.61 (12)
N4—Cr1—N390.20 (5)N1—C4—H4A110.0
N1—Cr1—N383.06 (5)C5—C4—H4A110.0
N5—Cr1—N2174.70 (5)N1—C4—H4B110.0
N6—Cr1—N286.73 (5)C5—C4—H4B110.0
N4—Cr1—N283.23 (5)H4A—C4—H4B108.3
N1—Cr1—N289.96 (5)N3—C5—C4107.65 (12)
N3—Cr1—N297.17 (5)N3—C5—H5A110.2
C4—N1—C1112.42 (11)C4—C5—H5A110.2
C4—N1—Cr1108.95 (9)N3—C5—H5B110.2
C1—N1—Cr1118.54 (9)C4—C5—H5B110.2
C4—N1—H1N1104.3 (13)H5A—C5—H5B108.5
C1—N1—H1N1105.8 (13)N2—C6—C7107.70 (12)
Cr1—N1—H1N1105.6 (13)N2—C6—H6A110.2
C6—N2—C3110.46 (12)C7—C6—H6A110.2
C6—N2—Cr1106.62 (9)N2—C6—H6B110.2
C3—N2—Cr1117.91 (9)C7—C6—H6B110.2
C6—N2—H1N2106.5 (14)H6A—C6—H6B108.5
C3—N2—H1N2106.1 (14)N4—C7—C6108.29 (12)
Cr1—N2—H1N2108.7 (14)N4—C7—H7A110.0
C8—N3—C5109.76 (12)C6—C7—H7A110.0
C8—N3—Cr1117.03 (10)N4—C7—H7B110.0
C5—N3—Cr1106.96 (10)C6—C7—H7B110.0
C8—N3—H1N3104.5 (13)H7A—C7—H7B108.4
C5—N3—H1N3105.0 (12)N3—C8—C9112.93 (13)
Cr1—N3—H1N3113.0 (13)N3—C8—H8A109.0
C7—N4—C10112.23 (12)C9—C8—H8A109.0
C7—N4—Cr1108.83 (9)N3—C8—H8B109.0
C10—N4—Cr1118.20 (10)C9—C8—H8B109.0
C7—N4—H1N4102.1 (12)H8A—C8—H8B107.8
C10—N4—H1N4106.4 (12)C10—C9—C8115.10 (13)
Cr1—N4—H1N4107.8 (12)C10—C9—H9A108.5
C11—N5—Cr1170.02 (13)C8—C9—H9A108.5
C12—N6—Cr1157.72 (12)C10—C9—H9B108.5
N1—C1—C2113.34 (12)C8—C9—H9B108.5
N1—C1—H1A108.9H9A—C9—H9B107.5
C2—C1—H1A108.9N4—C10—C9113.77 (13)
N1—C1—H1B108.9N4—C10—H10A108.8
C2—C1—H1B108.9C9—C10—H10A108.8
H1A—C1—H1B107.7N4—C10—H10B108.8
C3—C2—C1115.42 (12)C9—C10—H10B108.8
C3—C2—H2A108.4H10A—C10—H10B107.7
C1—C2—H2A108.4N5—C11—S3179.66 (15)
C3—C2—H2B108.4N6—C12—S2178.82 (14)
C1—C2—H2B108.4N7—C13—S4178.35 (14)
C4—N1—C1—C2−72.13 (15)C3—N2—C6—C7174.88 (12)
Cr1—N1—C1—C256.50 (15)Cr1—N2—C6—C745.63 (13)
N1—C1—C2—C3−64.97 (17)C10—N4—C7—C6169.85 (13)
C6—N2—C3—C2177.56 (12)Cr1—N4—C7—C637.10 (15)
Cr1—N2—C3—C2−59.54 (15)N2—C6—C7—N4−55.65 (16)
C1—C2—C3—N266.51 (17)C5—N3—C8—C9177.66 (13)
C1—N1—C4—C5169.43 (12)Cr1—N3—C8—C9−60.26 (16)
Cr1—N1—C4—C535.94 (14)N3—C8—C9—C1066.73 (19)
C8—N3—C5—C4173.69 (12)C7—N4—C10—C9−71.42 (17)
Cr1—N3—C5—C445.79 (14)Cr1—N4—C10—C956.52 (16)
N1—C4—C5—N3−54.89 (16)C8—C9—C10—N4−64.47 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···S2i0.86 (2)2.59 (2)3.4138 (15)160.1 (17)
N2—H1N2···S4ii0.77 (2)2.66 (2)3.3521 (14)149.8 (18)
N3—H1N3···N7ii0.834 (19)2.119 (19)2.9238 (19)162.0 (17)
N4—H1N4···N7iii0.851 (19)2.150 (19)2.947 (2)155.9 (17)
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula[Cr(NCS)2(C10H24N4)]NCS
Mr426.57
Crystal system, space groupMonoclinic, P21/c
Temperature (K)98
a, b, c (Å)10.590 (2), 7.6970 (15), 23.750 (5)
β (°) 94.70 (3)
V (Å3)1929.4 (7)
Z4
Radiation typeSynchrotron, λ = 0.740 Å
µ (mm−1)1.03
Crystal size (mm)0.01 × 0.01 × 0.01
Data collection
DiffractometerADSC Q210 CCD area-detector
Absorption correctionEmpirical (using intensity measurements)
(HKL-3000 SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.988, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		16587, 4727, 3998
Rint0.038
(sin θ/λ)max (Å−1)0.665
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.085, 1.07
No. of reflections4727
No. of parameters234
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.38, −0.46

Computer programs: ADSC Quantum-210 ADX (Arvai & Nielsen, 1983), HKL-3000 (Otwinowski & Minor, 1997), SHELXS2013 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), DIAMOND (Brandenburg, 2007), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···S2i0.86 (2)2.59 (2)3.4138 (15)160.1 (17)
N2—H1N2···S4ii0.77 (2)2.66 (2)3.3521 (14)149.8 (18)
N3—H1N3···N7ii0.834 (19)2.119 (19)2.9238 (19)162.0 (17)
N4—H1N4···N7iii0.851 (19)2.150 (19)2.947 (2)155.9 (17)
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

The research was supported by a grant from the 2012 Inter­national Academic Exchange Program of Andong National University. The experiment at PLS-II 2D-SMC beamline was supported in part by MEST and POSTECH.

References

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ISSN: 2056-9890
Volume 69| Part 7| July 2013| Pages m376-m377
https://doi.org/10.1107/S1600536813015456
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